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Synthesis of Sulfur‐Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction
Author(s) -
Liu Shuli,
Huang Chengting,
Zhang Jing,
Tian Siyu,
Li Chang,
Fu Nina,
Wang Lianhui,
Zhao Baomin,
Huang Wei
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900344
Subject(s) - chemistry , rearrangement reaction , cope rearrangement , sulfur , ring (chemistry) , retrosynthetic analysis , stereochemistry , smiles rearrangement , reaction conditions , catalysis , organic chemistry , total synthesis
We present herein a strategy towards the straightforward synthesis of a novel sulfur‐hybridized pyracylene, tetraceno[5,6‐bc:11,12‐b'c']dithiophene (TDT) derivatives, via 2‐fold FeCl 3 ‐mediated Scholl reaction. Surprisingly, the substituents on the precursors will guide the synthetic route, when the substituents were bromo‐ or phenyl‐, quantitatively debromination or phenyl ring shift mediated rearrangement were observed respectively, the rearrangement products were identified by the HR‐Mass and 2D NMR analyses. Additionally, a retrosynthetic method was adopted to confirm the unexpected reaction results in rearrangement of Scholl reaction.